Synthesis of Perdeuterated Alkyl Amines/Amides with Pt/C as Catalyst under Mild Conditions

Hong Hai Zhang; Meng Zhe Chen; Xinbin Yu; Peter V. Bonnesen; Zili Wu; Hsin Lung Chen; Hugh O’Neill

doi:10.1021/acs.joc.4c00553

Synthesis of Perdeuterated Alkyl Amines/Amides with Pt/C as Catalyst under Mild Conditions

Hong Hai Zhang, Meng Zhe Chen, Xinbin Yu, Peter V. Bonnesen, Zili Wu, Hsin Lung Chen, Hugh O’Neill

Research output: Contribution to journal › Article › peer-review

1 Scopus citations

Abstract

A convenient method for the synthesis of perdeuterated alkyl amides/amines is disclosed. Perdeuterated acetyl amides can be achieved by a hydrogen-deuterium (H/D) exchange protocol with Pt/C as a catalyst and D₂O as a deuterium source under mild conditions. After removal or reduction of the acetyl group, this protocol can provide perdeuterated primary, secondary, and tertiary amines, which are difficult to achieve via other methods.

Original language	English
Pages (from-to)	8262-8266
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	89
Issue number	11
DOIs	https://doi.org/10.1021/acs.joc.4c00553
State	Published - Jun 7 2024

Funding

The organic reactions were conducted at the Center for Nanophase Materials Sciences, which is a DOE Office of Science User Facility operated by the Oak Ridge National Laboratory. Dr. Hong-Hai Zhang is supported by the Center for Structural Molecular Biology, sponsored by the Office of Biological and Environmental Research.

Access to Document

10.1021/acs.joc.4c00553

Cite this

@article{28de4089a6fe4dfc8fc60e7854bcbe87,

title = "Synthesis of Perdeuterated Alkyl Amines/Amides with Pt/C as Catalyst under Mild Conditions",

abstract = "A convenient method for the synthesis of perdeuterated alkyl amides/amines is disclosed. Perdeuterated acetyl amides can be achieved by a hydrogen-deuterium (H/D) exchange protocol with Pt/C as a catalyst and D2O as a deuterium source under mild conditions. After removal or reduction of the acetyl group, this protocol can provide perdeuterated primary, secondary, and tertiary amines, which are difficult to achieve via other methods.",

author = "Zhang, {Hong Hai} and Chen, {Meng Zhe} and Xinbin Yu and Bonnesen, {Peter V.} and Zili Wu and Chen, {Hsin Lung} and Hugh O{\textquoteright}Neill",

note = "Publisher Copyright: {\textcopyright} 2024 American Chemical Society",

year = "2024",

month = jun,

day = "7",

doi = "10.1021/acs.joc.4c00553",

language = "English",

volume = "89",

pages = "8262--8266",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "11",

}

TY - JOUR

T1 - Synthesis of Perdeuterated Alkyl Amines/Amides with Pt/C as Catalyst under Mild Conditions

AU - Zhang, Hong Hai

AU - Chen, Meng Zhe

AU - Yu, Xinbin

AU - Bonnesen, Peter V.

AU - Wu, Zili

AU - Chen, Hsin Lung

AU - O’Neill, Hugh

PY - 2024/6/7

Y1 - 2024/6/7

N2 - A convenient method for the synthesis of perdeuterated alkyl amides/amines is disclosed. Perdeuterated acetyl amides can be achieved by a hydrogen-deuterium (H/D) exchange protocol with Pt/C as a catalyst and D2O as a deuterium source under mild conditions. After removal or reduction of the acetyl group, this protocol can provide perdeuterated primary, secondary, and tertiary amines, which are difficult to achieve via other methods.

AB - A convenient method for the synthesis of perdeuterated alkyl amides/amines is disclosed. Perdeuterated acetyl amides can be achieved by a hydrogen-deuterium (H/D) exchange protocol with Pt/C as a catalyst and D2O as a deuterium source under mild conditions. After removal or reduction of the acetyl group, this protocol can provide perdeuterated primary, secondary, and tertiary amines, which are difficult to achieve via other methods.

UR - http://www.scopus.com/inward/record.url?scp=85193058255&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.4c00553

DO - 10.1021/acs.joc.4c00553

M3 - Article

AN - SCOPUS:85193058255

SN - 0022-3263

VL - 89

SP - 8262

EP - 8266

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 11

ER -

Synthesis of Perdeuterated Alkyl Amines/Amides with Pt/C as Catalyst under Mild Conditions

Abstract

Funding

Access to Document

Other files and links

Fingerprint

Cite this